HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2039815Generated: October 25, 2026
8-Hydroxyquinoline → 1-Phenyl-1H-pyrrolo[3,2-b]pyridine
https://huagongshe.com/reaction/2039815
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 8-Hydroxyquinoline | HCID 1923 | — |
| Reactant | 4-Azaindole | HCID 9226 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Iodobenzene | HCID 11575 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-Phenyl-1H-pyrrolo[3,2-b]pyridine | HCID 21083963 | 188.4% |
Reaction Steps
To a mixture of 4-azaindole (1.20 g, 10.2 mmol), copper(I) iodide (290 mg, 1.53 mmol), 8-hydroxyquinoline (221 mg, 1.53 mmol) and potassium carbonate (1.55 g, 11.2 mmol) in DMSO (24 ml) was added iodobenzene (1.25 ml, 11.2 mmol). The reaction mixture was stirred at 130° C. for 3 h. The mixture was then cooled to room temperature and a solution of ammonium hydroxide (10% in water) and EA were added. The organic layer was separated, washed twice with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. Column chromatography on silica gel (EA/HEP) gave 560 mg of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08580813B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-81bb0f9394474220ae56e786b368d364 |
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| Source note | uspto-grants-2013_11 |
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